How to Spend 48 Hours in Chicago

Todd about Town: Our travel and entertainment editor offers one way to stay, explore, and dine in the Windy City


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It had been a few years since I visited the Windy City, so when I received an invitation to stay at Chicago’s InterContinental Hotel on the Miracle Mile, I decided it was time to pay a return visit. During the one-hour trip from the Minneapolis-St. Paul International Airport to Chicago’s O’Hare Airport, you barely have enough time to finish your coffee before landing.

Day #1

If you’re visiting the InterContinental Hotel, ask the concierge about the audio walking tour. The 42-story Art Deco hotel has strong Egyptian and Greek influences, with ornate carvings and paintings, and I was surprised to learn it’s the only Michigan Avenue property with a front entrance on the Miracle Mile. The 14th-floor swimming pool, in Spanish Renaissance style, was considered an engineering marvel when it was built, as it was one of the highest indoor pools in the world. Olympic athlete and actor Johnny Weissmuller, who played Tarzan in the ’30s and ’40s, trained there.

Next, I headed to Vertiport Chicago for a helicopter tour of the city. For holiday shopping, consider taking the holiday lights tour, available from November 17 to January 6. Tickets for the helicopter tour can be purchased online or at kiosks at the Lincoln Park Zoo and at Millennium Park. A Vertiport luxury car will transport you to and from the heliport.


Flying over the Chicago Bears Football Stadium

After the tour, I returned to the hotel for an evening of fine dining at Michael Jordan’s Restaurant, located on the hotel’s second floor. From the double-smoked bacon appetizer to the M.J.’s Delmonico USDA Prime Steak and the mashed potato trio of lobster, sweet potato brûlée, and roasted onion and gruyères, this place was an absolute slam dunk.


bacon, as an appetizer? Double-smoked and delicious at Michael Jordan's Restaurant.


M.J.'s Delmonico USDA Prime Steak

And, yes, you can expect the Chicago Bulls player’s number, 23, to appear in many clever ways throughout the restaurant, including in the signature cocktails and the mouth-dropping 23-layer chocolate cake.


Michael Jordan's famous silhouette, gracing the froth on a cocktail


Count 'em: the decadent 23-layer chocolate cake.

After dinner, I headed out to stroll Michigan Avenue in hopes of putting a dent in the 23-plus pounds I likely gained at Michael Jordan’s.

Day # 2

I hit up the hotel’s gym for some guilt-induced cardio, then the spa for a relaxing massage. With a referral from my Fox 9 pal Jason Mathison, I headed to lunch at Imperial Lamian for authentic Chinese. The experience did not disappoint. Imperial Lamian is unlike any other restaurants I have visited outside of Beijing and Shanghai. If you go, be sure to try a dish made with the restaurant’s hand-pulled noodles, prepared onsite in an open kitchen. I tried many of the menu items, and I must say the rainbow-colored soup dumplings are over-the-top delicious and a must-order. (I have since passed on the recommendation to friends visiting Chicago, and they have all given Imperial Lamian two thumbs up as well.)


The Rainbow Dumplings at Imperial Lamian

After lunch, I met my guide from Inside Chicago for an architecture walking tour of the city, one of the most informative and entertaining walking tours I have taken domestically or internationally. Our seasoned guide, Hillary Marzec, walked us through the downtown neighborhoods.

The lively history discussion continued at the Eno wine bar, for a wine tasting inside the InterContinental Hotel, presented by the house sommelier Mark Canak. And you can’ t leave Chicago without stopping at a jazz club. I headed to Andy’s Jazz Club in the River North area for some live music and a pint of local brew: a Goose Island IPA.

The next day, it was time to head back. Wheels up to wheels down, time in the air was, again, under 60 minutes. If you’re looking for a quick getaway with abundant history, entertainment, and dining, Chicago is your answer.

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Whether you are a seasoned Twin Cities traveler or planning your first trip to Minnesota, this blog will introduce you to many new adventures to add to your itinerary. From day trips and scenic discoveries to luxurious girls weekends, travel tips, and insider scoops, our editors will give you all the information you need to enjoy your stay Up North.

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